Tetrahydrofuran-2,5-dicarbaldehydes (diformyl-tetrahydrofuran, dfthf) and process for making the same
AssigneeArcher Daniels Midland Company
InventorKenneth Stensrud
Life of this patent
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Abstract
Tetrahydrofuran-(THF)-2,5-dicarbaldehyde and a process of preparing the same are described. The process involves reacting THF-diols in an inert organic solvent with an oxidizing agent at a temperature up to about 50 C. The process can use either HMF or THF-diols as starting materials, and enables a single-step conversion of THF-diols into a precursor material that can be transformed into a multitude of furanic derivative compounds. THF dicarbaldehyde can be modified according to certain reaction processes to generate either new or existing derivative compounds.
Claims31
A process of making a tetrahydrofuran-(THF)-2,5-dicarbaldehyde, comprising:
- providing a reaction mixture containing THF-diols and an inert organic solvent;
- reacting said THF-diols with an oxidizing agent at a reaction temperature between about 10° C. to about 50° C., in a non-inert atmosphere.
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A tetrahydrofuran (THF)-2,5-dicarbaldehyde:
A method of preparing a furanic derivative compound of a tetrahydrofuran (THF)-2,5-dialdehyde comprising:
- reacting a mixture containing THF-diols and an inert organic solvent with an oxidizing agent at a reaction temperature up to about 50° C., in a non-inert atmosphere;
- and transforming said THF-dicarbaldehyde into a furanic derivative compound.
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A furanic derivative compound transformed according to the anyone of the following reactions:
- wherein [O] is oxidation, R′H, alkyl, alkenyl, alkynyl, or aryl species.
A furanic derivative compound transformed by at least one of the following:
- a) oxidation;
- b) Schiff-base modification, having a general formula:
- where R is a H, alkyl, alkenyl, alkynyl, or aryl species;
- c) sulfonimidation, having a general formula:
- where R is a H, alkyl, alkenyl, alkynyl, or aryl species;
- d) synthesis of mono- and diacetals, having a general formula:
- where R is a H, alkyl, alkenyl, alkynyl, or aryl species;
- e) reductive amination, having a general formula
- where R is a H, alkyl, alkenyl, alkynyl, or aryl species;
- f) Aldol condensation, having a general formula:
- g) Aldol addition, having a general formula:
- where R is a H, alkyl, alkenyl, alkynyl, or aryl species;
- h) formation of oxime, having a general formula:
- where R is a H, alkyl, alkenyl, alkynyl, or aryl species;
- or i) a Wittig reaction.
Dependencies are inferred from the claim text.